HCID 86610044, compound → HCID 86610043, compound

HRID 490284Notes

Reaction equation

HRID 490284 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)[CH:5]=[CH:4][CH:3]=1>CC(O)C.Br.CC(O)=O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86610044HCID 86610044, compound

Product 1

HCID 86610043HCID 86610043, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A mixture of (±)-1,1-dimethylethyl 4-[[1-[(6-bromo-2-pyridinyl)ethoxymethyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (0.0026 mol) in 2-propanol (30 ml) and HBr/CH3COOH (2 ml) was stirred and refluxed for 2 hours and then cooled. The solvent was evaporated. The residue was taken up in H2O and CH2Cl2. The mixture was alkalized with a NaOH solution. The organic layer was separated, washed with H2O, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/NH3 90/10). The pure fractions were collected and the solvent was evaporated. The residue was suspended in petroleum ether. The precipitate was filtered off and dried. This fraction was recrystallized from a small amount of CH3CN. The precipitate was filtered off and dried, yielding 0.22 g of (±)-1-[(6-bromo-2-pyridinyl)ethoxymethyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine (19.6%) (compound 4).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. washwashed with H2O
  6. customdried
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/NH3 90/10)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. filtrationThe precipitate was filtered off
  13. customdried
  14. customThis fraction was recrystallized from a small amount of CH3CN
  15. filtrationThe precipitate was filtered off
  16. customdried

Sources & evidence

ORD record
ord-44bf616281b44e6ab8a283b5c0b4459e
Source dataset
uspto-grants-2009_05
Patent number
US07528149B2

Reaction notes

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